Typical yearly costs of owning a 27' boat might be:
$1500 for hauling, winter storage and splash
for a mooring, as low as
$300 to $$$
or as high as:
$3500 for a slip for the summer.
Insurance: ~$350-500
Registration: $80
============
X,XXX.xx
That is your minimum budget for the year.

I think that donna makes some good points. You have to find the boat that speaks to you (and your wife or gf).
Bigger boats do cost more as everything is priced by the length of the boat. 27' feet is a good size to start in that can still be single handed and allow for some overnight trips.

There are quite a number of boat makes in your price range near 27' (Catalina, Tartan, O'day, Hunter, Bristol ....). I'm partial to the Tartan 27' having owned one for 10 years.

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